NPASS Compound

Structure

NPC475255 OpenBabel07101719152D 34 37 0 0 1 0 0 0 0 0999 V2000 9.5575 -2.1473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0928 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0102 -1.5803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6910 -3.0229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -5.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0827 -3.2742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9781 -4.2688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -7.0748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -4.4767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -6.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -3.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3986 -0.8601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7044 -1.2202 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -7.9408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -6.2087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3496 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9612 -1.8894 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.6554 -1.5292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -7.9408 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -5.3427 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.1691 -2.8675 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 6.0000 -4.4767 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.5000 -5.3427 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -7.0748 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -7.0748 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5000 -3.6107 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 4.0000 -6.2087 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.8633 -2.5074 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.9408 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -7.8068 0.0000 O 0 5 0 0 0 0 0 0 0 0 0 0 0.5000 -8.8068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -9.8068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -8.8068 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -8.8068 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 16 1 0 0 0 0 3 17 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 7 1 0 0 0 0 6 21 1 0 0 0 0 7 22 1 0 0 0 0 8 10 1 0 0 0 0 8 19 1 0 0 0 0 9 11 1 0 0 0 0 9 23 2 0 0 0 0 10 27 1 0 0 0 0 11 26 1 0 0 0 0 12 16 2 0 0 0 0 12 18 1 0 0 0 0 13 17 1 0 0 0 0 13 18 1 0 0 0 0 14 19 1 0 0 0 0 14 24 1 0 0 0 0 15 20 1 0 0 0 0 15 25 1 0 0 0 0 17 21 1 0 0 0 0 18 28 2 0 0 0 0 19 33 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 22 26 1 0 0 0 0 23 27 1 0 0 0 0 24 25 1 0 0 0 0 24 27 1 0 0 0 0 25 29 1 0 0 0 0 30 34 1 0 0 0 0 31 34 2 0 0 0 0 32 34 2 0 0 0 0 33 34 1 0 0 0 0 M CHG 1 30 -1 M END $$$$

Physi-Chem Properties

Molecular Weight:	493.26
Volume:	503.345
LogP:	4.243
LogD:	3.982
LogS:	-4.912
# Rotatable Bonds:	6
TPSA:	103.73
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.243
Synthetic Accessibility Score:	5.193
Fsp3:	0.815
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.757
MDCK Permeability:	2.0172246877336875e-05
Pgp-inhibitor:	0.988
Pgp-substrate:	0.012
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.447
Plasma Protein Binding (PPB):	94.74920654296875%
Volume Distribution (VD):	1.099
Pgp-substrate:	3.4088997840881348%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.75
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.898
CYP2C9-inhibitor:	0.083
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.145
CYP3A4-inhibitor:	0.232
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	5.235
Half-life (T1/2):	0.028

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.756
Drug-inuced Liver Injury (DILI):	0.318
AMES Toxicity:	0.343
Rat Oral Acute Toxicity:	0.91
Maximum Recommended Daily Dose:	0.967
Skin Sensitization:	0.973
Carcinogencity:	0.91
Eye Corrosion:	0.875
Eye Irritation:	0.655
Respiratory Toxicity:	0.988

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC475255

Natural Product ID:	NPC475255
*Common Name:**	3-O-Sulfomarthasterone
IUPAC Name:	sodium;[(3S,5S,6S,8S,10S,13R,14S,17R)-6-hydroxy-10,13-dimethyl-17-[(2R)-6-methyl-4-oxohept-5-en-2-yl]-2,3,4,5,6,7,8,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] sulfate
Synonyms:	3-O-Sulfomarthasterone
Standard InCHIKey:	WEQSEBSGCCAXTM-FJSUMNSHSA-M
Standard InCHI:	InChI=1S/C27H42O6S.Na/c1-16(2)12-18(28)13-17(3)21-6-7-22-20-15-25(29)24-14-19(33-34(30,31)32)8-10-27(24,5)23(20)9-11-26(21,22)4;/h9,12,17,19-22,24-25,29H,6-8,10-11,13-15H2,1-5H3,(H,30,31,32);/q;+1/p-1/t17-,19+,20+,21-,22+,24-,25+,26-,27-;/m1./s1
SMILES:	CC(=CC(=O)C[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC=C1[C@H]2C[C@@H]([C@@H]2[C@]1(C)CC[C@@H](C2)OS(=O)(=O)[O-])O)C)C.[Na+]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL502136
PubChem CID:	23714728
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003566] Cholestane steroids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473430]
NPO9446	Asterias rathbuni	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Inhibition	=	100.0	%	PMID[469192]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC475255 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	166
0.1-0.2	1229
0.2-0.3	5221
0.3-0.4	14321
0.4-0.5	8324
0.5-0.6	5857
0.6-0.7	4986
0.7-0.8	2302
0.8-0.85	206
0.85-0.9	68
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9222	High Similarity	NPC111015
0.9205	High Similarity	NPC1015
0.9205	High Similarity	NPC31985
0.9195	High Similarity	NPC475740
0.9186	High Similarity	NPC470574
0.9091	High Similarity	NPC328539
0.9091	High Similarity	NPC471722
0.908	High Similarity	NPC474778
0.908	High Similarity	NPC72133
0.908	High Similarity	NPC31564
0.908	High Similarity	NPC145879
0.908	High Similarity	NPC474733
0.908	High Similarity	NPC474732
0.907	High Similarity	NPC214043
0.907	High Similarity	NPC85774
0.9011	High Similarity	NPC245972
0.9011	High Similarity	NPC196485
0.9	High Similarity	NPC185936
0.9	High Similarity	NPC168027
0.9	High Similarity	NPC473998
0.9	High Similarity	NPC272746
0.8989	High Similarity	NPC309603
0.8989	High Similarity	NPC275740
0.8989	High Similarity	NPC86319
0.8989	High Similarity	NPC473999
0.8977	High Similarity	NPC58063
0.8966	High Similarity	NPC197823
0.8889	High Similarity	NPC48010
0.8889	High Similarity	NPC191684
0.8889	High Similarity	NPC126993
0.8889	High Similarity	NPC85173
0.8876	High Similarity	NPC131470
0.8876	High Similarity	NPC143767
0.8851	High Similarity	NPC59453
0.8851	High Similarity	NPC221758
0.8851	High Similarity	NPC473246
0.8804	High Similarity	NPC8993
0.8791	High Similarity	NPC155304
0.8791	High Similarity	NPC475806
0.8778	High Similarity	NPC186688
0.8778	High Similarity	NPC268406
0.8778	High Similarity	NPC32830
0.8778	High Similarity	NPC474245
0.8778	High Similarity	NPC475921
0.8778	High Similarity	NPC474704
0.8778	High Similarity	NPC119416
0.8778	High Similarity	NPC477943
0.8778	High Similarity	NPC26959
0.8764	High Similarity	NPC474684
0.8764	High Similarity	NPC142361
0.8764	High Similarity	NPC141292
0.875	High Similarity	NPC469948
0.8737	High Similarity	NPC154072
0.8723	High Similarity	NPC108078
0.8723	High Similarity	NPC18509
0.871	High Similarity	NPC271195
0.8696	High Similarity	NPC12722
0.8696	High Similarity	NPC470375
0.8696	High Similarity	NPC69454
0.8696	High Similarity	NPC470376
0.8696	High Similarity	NPC478129
0.8681	High Similarity	NPC183283
0.8667	High Similarity	NPC193360
0.8667	High Similarity	NPC471724
0.8667	High Similarity	NPC292491
0.8667	High Similarity	NPC310752
0.8667	High Similarity	NPC470417
0.8652	High Similarity	NPC51014
0.8652	High Similarity	NPC118648
0.8652	High Similarity	NPC94755
0.8652	High Similarity	NPC222613
0.8652	High Similarity	NPC475022
0.8636	High Similarity	NPC321187
0.8636	High Similarity	NPC161423
0.8636	High Similarity	NPC227064
0.8636	High Similarity	NPC478102
0.8636	High Similarity	NPC82902
0.8636	High Similarity	NPC329043
0.8636	High Similarity	NPC472265
0.8636	High Similarity	NPC25833
0.8636	High Similarity	NPC237712
0.8636	High Similarity	NPC58841
0.8621	High Similarity	NPC328351
0.8621	High Similarity	NPC151519
0.8617	High Similarity	NPC249954
0.8617	High Similarity	NPC192428
0.8602	High Similarity	NPC166906
0.8587	High Similarity	NPC212301
0.8587	High Similarity	NPC110657
0.8587	High Similarity	NPC189520
0.8587	High Similarity	NPC233116
0.8587	High Similarity	NPC63748
0.8587	High Similarity	NPC86266
0.8571	High Similarity	NPC77263
0.8571	High Similarity	NPC250592
0.8556	High Similarity	NPC93778
0.8556	High Similarity	NPC187376
0.8556	High Similarity	NPC90652
0.8556	High Similarity	NPC317590
0.8556	High Similarity	NPC159046
0.8556	High Similarity	NPC233836
0.8542	High Similarity	NPC144956
0.8539	High Similarity	NPC474218
0.8539	High Similarity	NPC471224
0.8526	High Similarity	NPC190554
0.8511	High Similarity	NPC317586
0.8511	High Similarity	NPC259286
0.8511	High Similarity	NPC473170
0.8511	High Similarity	NPC470016
0.8495	Intermediate Similarity	NPC170220
0.8495	Intermediate Similarity	NPC107674
0.8495	Intermediate Similarity	NPC472930
0.8495	Intermediate Similarity	NPC474807
0.8495	Intermediate Similarity	NPC141497
0.8478	Intermediate Similarity	NPC171441
0.8478	Intermediate Similarity	NPC471896
0.8462	Intermediate Similarity	NPC474677
0.8462	Intermediate Similarity	NPC53911
0.8462	Intermediate Similarity	NPC472802
0.8462	Intermediate Similarity	NPC328313
0.8462	Intermediate Similarity	NPC242864
0.8444	Intermediate Similarity	NPC155011
0.8444	Intermediate Similarity	NPC158393
0.8444	Intermediate Similarity	NPC327115
0.8444	Intermediate Similarity	NPC55309
0.8444	Intermediate Similarity	NPC28252
0.8444	Intermediate Similarity	NPC469994
0.8438	Intermediate Similarity	NPC114274
0.8438	Intermediate Similarity	NPC103051
0.8427	Intermediate Similarity	NPC33913
0.8421	Intermediate Similarity	NPC305483
0.8421	Intermediate Similarity	NPC96859
0.8421	Intermediate Similarity	NPC328162
0.8409	Intermediate Similarity	NPC48362
0.8404	Intermediate Similarity	NPC474690
0.8404	Intermediate Similarity	NPC49670
0.8404	Intermediate Similarity	NPC299100
0.8391	Intermediate Similarity	NPC2482
0.8391	Intermediate Similarity	NPC472478
0.8387	Intermediate Similarity	NPC233455
0.8387	Intermediate Similarity	NPC4036
0.8387	Intermediate Similarity	NPC65120
0.8387	Intermediate Similarity	NPC131872
0.8387	Intermediate Similarity	NPC154101
0.8387	Intermediate Similarity	NPC23434
0.8387	Intermediate Similarity	NPC158030
0.8387	Intermediate Similarity	NPC297265
0.8387	Intermediate Similarity	NPC145067
0.837	Intermediate Similarity	NPC310010
0.837	Intermediate Similarity	NPC84271
0.837	Intermediate Similarity	NPC472983
0.837	Intermediate Similarity	NPC102414
0.837	Intermediate Similarity	NPC77168
0.837	Intermediate Similarity	NPC326627
0.837	Intermediate Similarity	NPC76879
0.8367	Intermediate Similarity	NPC22388
0.8367	Intermediate Similarity	NPC477915
0.8352	Intermediate Similarity	NPC96496
0.8352	Intermediate Similarity	NPC136548
0.8352	Intermediate Similarity	NPC138756
0.8351	Intermediate Similarity	NPC15390
0.8333	Intermediate Similarity	NPC76518
0.8333	Intermediate Similarity	NPC320306
0.8333	Intermediate Similarity	NPC474083
0.8333	Intermediate Similarity	NPC253826
0.8333	Intermediate Similarity	NPC478127
0.8333	Intermediate Similarity	NPC133954
0.8316	Intermediate Similarity	NPC45324
0.8316	Intermediate Similarity	NPC222845
0.8316	Intermediate Similarity	NPC162001
0.8316	Intermediate Similarity	NPC139570
0.8316	Intermediate Similarity	NPC472485
0.8316	Intermediate Similarity	NPC280725
0.8316	Intermediate Similarity	NPC180950
0.8316	Intermediate Similarity	NPC88310
0.8315	Intermediate Similarity	NPC475726
0.8315	Intermediate Similarity	NPC278648
0.8315	Intermediate Similarity	NPC476082
0.8315	Intermediate Similarity	NPC472743
0.83	Intermediate Similarity	NPC296945
0.83	Intermediate Similarity	NPC85829
0.83	Intermediate Similarity	NPC202167
0.83	Intermediate Similarity	NPC260268
0.83	Intermediate Similarity	NPC150531
0.83	Intermediate Similarity	NPC49958
0.83	Intermediate Similarity	NPC302607
0.83	Intermediate Similarity	NPC152695
0.83	Intermediate Similarity	NPC476027
0.83	Intermediate Similarity	NPC97202
0.83	Intermediate Similarity	NPC214264
0.83	Intermediate Similarity	NPC48733
0.83	Intermediate Similarity	NPC319077
0.83	Intermediate Similarity	NPC50692
0.83	Intermediate Similarity	NPC171137
0.8298	Intermediate Similarity	NPC272075
0.8298	Intermediate Similarity	NPC214756
0.8298	Intermediate Similarity	NPC470224
0.8298	Intermediate Similarity	NPC295643
0.8298	Intermediate Similarity	NPC134826
0.8298	Intermediate Similarity	NPC109305

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC475255 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	139
0.1-0.2	1473
0.2-0.3	4136
0.3-0.4	2410
0.4-0.5	530
0.5-0.6	149
0.6-0.7	122
0.7-0.8	132
0.8-0.85	38
0.85-0.9	19
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9205	High Similarity	NPD5328	Approved
0.908	High Similarity	NPD3618	Phase 1
0.9	High Similarity	NPD6079	Approved
0.8901	High Similarity	NPD4202	Approved
0.8851	High Similarity	NPD4786	Approved
0.8723	High Similarity	NPD4755	Approved
0.8636	High Similarity	NPD3666	Approved
0.8636	High Similarity	NPD3133	Approved
0.8636	High Similarity	NPD3665	Phase 1
0.8636	High Similarity	NPD3668	Phase 3
0.8621	High Similarity	NPD3667	Approved
0.8617	High Similarity	NPD5221	Approved
0.8617	High Similarity	NPD4697	Phase 3
0.8617	High Similarity	NPD5220	Clinical (unspecified phase)
0.8617	High Similarity	NPD5222	Approved
0.8542	High Similarity	NPD5286	Approved
0.8542	High Similarity	NPD5285	Approved
0.8542	High Similarity	NPD4700	Approved
0.8542	High Similarity	NPD4696	Approved
0.8526	High Similarity	NPD5173	Approved
0.8469	Intermediate Similarity	NPD4754	Approved
0.8454	Intermediate Similarity	NPD5223	Approved
0.8387	Intermediate Similarity	NPD7515	Phase 2
0.837	Intermediate Similarity	NPD4753	Phase 2
0.8367	Intermediate Similarity	NPD5224	Approved
0.8367	Intermediate Similarity	NPD5226	Approved
0.8367	Intermediate Similarity	NPD5225	Approved
0.8367	Intermediate Similarity	NPD4633	Approved
0.8367	Intermediate Similarity	NPD5211	Phase 2
0.83	Intermediate Similarity	NPD5739	Approved
0.83	Intermediate Similarity	NPD6675	Approved
0.83	Intermediate Similarity	NPD6402	Approved
0.83	Intermediate Similarity	NPD7128	Approved
0.8298	Intermediate Similarity	NPD6399	Phase 3
0.8283	Intermediate Similarity	NPD5174	Approved
0.8283	Intermediate Similarity	NPD5175	Approved
0.8242	Intermediate Similarity	NPD5279	Phase 3
0.8202	Intermediate Similarity	NPD4223	Phase 3
0.8202	Intermediate Similarity	NPD4221	Approved
0.82	Intermediate Similarity	NPD5141	Approved
0.8182	Intermediate Similarity	NPD7525	Registered
0.8137	Intermediate Similarity	NPD7320	Approved
0.8137	Intermediate Similarity	NPD6899	Approved
0.8137	Intermediate Similarity	NPD6881	Approved
0.8132	Intermediate Similarity	NPD5329	Approved
0.8119	Intermediate Similarity	NPD4768	Approved
0.8119	Intermediate Similarity	NPD4767	Approved
0.8077	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.8058	Intermediate Similarity	NPD6372	Approved
0.8058	Intermediate Similarity	NPD6373	Approved
0.8043	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD5701	Approved
0.8039	Intermediate Similarity	NPD5697	Approved
0.8022	Intermediate Similarity	NPD4197	Approved
0.8021	Intermediate Similarity	NPD7748	Approved
0.7981	Intermediate Similarity	NPD7290	Approved
0.7981	Intermediate Similarity	NPD5135	Approved
0.7981	Intermediate Similarity	NPD7102	Approved
0.7981	Intermediate Similarity	NPD6883	Approved
0.7981	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD6011	Approved
0.7961	Intermediate Similarity	NPD4730	Approved
0.7961	Intermediate Similarity	NPD4729	Approved
0.7961	Intermediate Similarity	NPD5128	Approved
0.7959	Intermediate Similarity	NPD6084	Phase 2
0.7959	Intermediate Similarity	NPD7902	Approved
0.7959	Intermediate Similarity	NPD6083	Phase 2
0.7938	Intermediate Similarity	NPD5210	Approved
0.7938	Intermediate Similarity	NPD4629	Approved
0.7935	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD6869	Approved
0.7905	Intermediate Similarity	NPD6649	Approved
0.7905	Intermediate Similarity	NPD6847	Approved
0.7905	Intermediate Similarity	NPD6650	Approved
0.7905	Intermediate Similarity	NPD6617	Approved
0.7905	Intermediate Similarity	NPD8130	Phase 1
0.7885	Intermediate Similarity	NPD6012	Approved
0.7885	Intermediate Similarity	NPD6013	Approved
0.7885	Intermediate Similarity	NPD6014	Approved
0.7872	Intermediate Similarity	NPD6672	Approved
0.7872	Intermediate Similarity	NPD5737	Approved
0.7849	Intermediate Similarity	NPD4688	Approved
0.7849	Intermediate Similarity	NPD7146	Approved
0.7849	Intermediate Similarity	NPD4693	Phase 3
0.7849	Intermediate Similarity	NPD4690	Approved
0.7849	Intermediate Similarity	NPD6684	Approved
0.7849	Intermediate Similarity	NPD7521	Approved
0.7849	Intermediate Similarity	NPD7334	Approved
0.7849	Intermediate Similarity	NPD5205	Approved
0.7849	Intermediate Similarity	NPD4138	Approved
0.7849	Intermediate Similarity	NPD6409	Approved
0.7849	Intermediate Similarity	NPD5330	Approved
0.7849	Intermediate Similarity	NPD4689	Approved
0.783	Intermediate Similarity	NPD6882	Approved
0.783	Intermediate Similarity	NPD8297	Approved
0.7816	Intermediate Similarity	NPD6942	Approved
0.7816	Intermediate Similarity	NPD7339	Approved
0.781	Intermediate Similarity	NPD4634	Approved
0.781	Intermediate Similarity	NPD5249	Phase 3
0.781	Intermediate Similarity	NPD5247	Approved
0.781	Intermediate Similarity	NPD5248	Approved
0.781	Intermediate Similarity	NPD5250	Approved
0.781	Intermediate Similarity	NPD5169	Approved
0.781	Intermediate Similarity	NPD5251	Approved
0.7788	Intermediate Similarity	NPD5168	Approved
0.7753	Intermediate Similarity	NPD3617	Approved
0.7736	Intermediate Similarity	NPD5216	Approved
0.7736	Intermediate Similarity	NPD5127	Approved
0.7736	Intermediate Similarity	NPD5215	Approved
0.7736	Intermediate Similarity	NPD5217	Approved
0.7717	Intermediate Similarity	NPD4788	Approved
0.77	Intermediate Similarity	NPD7638	Approved
0.7684	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7684	Intermediate Similarity	NPD6903	Approved
0.766	Intermediate Similarity	NPD5690	Phase 2
0.766	Intermediate Similarity	NPD4694	Approved
0.766	Intermediate Similarity	NPD5280	Approved
0.7653	Intermediate Similarity	NPD7900	Approved
0.7653	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7629	Intermediate Similarity	NPD5281	Approved
0.7629	Intermediate Similarity	NPD5284	Approved
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7624	Intermediate Similarity	NPD7640	Approved
0.7624	Intermediate Similarity	NPD7639	Approved
0.7593	Intermediate Similarity	NPD4632	Approved
0.7582	Intermediate Similarity	NPD4695	Discontinued
0.7576	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD5695	Phase 3
0.7558	Intermediate Similarity	NPD4747	Approved
0.7545	Intermediate Similarity	NPD6317	Approved
0.7528	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7525	Intermediate Similarity	NPD5696	Approved
0.7524	Intermediate Similarity	NPD6412	Phase 2
0.7523	Intermediate Similarity	NPD5167	Approved
0.7477	Intermediate Similarity	NPD6335	Approved
0.7473	Intermediate Similarity	NPD4195	Approved
0.7471	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD6274	Approved
0.7455	Intermediate Similarity	NPD6868	Approved
0.7444	Intermediate Similarity	NPD6116	Phase 1
0.7442	Intermediate Similarity	NPD4137	Phase 3
0.7429	Intermediate Similarity	NPD6008	Approved
0.7423	Intermediate Similarity	NPD6904	Approved
0.7423	Intermediate Similarity	NPD6673	Approved
0.7423	Intermediate Similarity	NPD6080	Approved
0.7411	Intermediate Similarity	NPD7101	Approved
0.7411	Intermediate Similarity	NPD7100	Approved
0.7387	Intermediate Similarity	NPD6009	Approved
0.7387	Intermediate Similarity	NPD7115	Discovery
0.7356	Intermediate Similarity	NPD4691	Approved
0.7353	Intermediate Similarity	NPD5290	Discontinued
0.7345	Intermediate Similarity	NPD6054	Approved
0.7345	Intermediate Similarity	NPD6059	Approved
0.7333	Intermediate Similarity	NPD6117	Approved
0.7321	Intermediate Similarity	NPD6313	Approved
0.7321	Intermediate Similarity	NPD6314	Approved
0.7303	Intermediate Similarity	NPD5733	Approved
0.7292	Intermediate Similarity	NPD4623	Approved
0.7292	Intermediate Similarity	NPD4519	Discontinued
0.7283	Intermediate Similarity	NPD7645	Phase 2
0.7281	Intermediate Similarity	NPD6908	Approved
0.7281	Intermediate Similarity	NPD6909	Approved
0.7281	Intermediate Similarity	NPD6291	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6370	Approved
0.7193	Intermediate Similarity	NPD6319	Approved
0.7174	Intermediate Similarity	NPD6118	Approved
0.7174	Intermediate Similarity	NPD6115	Approved
0.7174	Intermediate Similarity	NPD6114	Approved
0.7174	Intermediate Similarity	NPD6697	Approved
0.7172	Intermediate Similarity	NPD4096	Approved
0.7155	Intermediate Similarity	NPD6067	Discontinued
0.7155	Intermediate Similarity	NPD7604	Phase 2
0.7143	Intermediate Similarity	NPD5208	Approved
0.713	Intermediate Similarity	NPD6016	Approved
0.713	Intermediate Similarity	NPD5983	Phase 2
0.713	Intermediate Similarity	NPD6015	Approved
0.7129	Intermediate Similarity	NPD6001	Approved
0.7128	Intermediate Similarity	NPD4692	Approved
0.7128	Intermediate Similarity	NPD4139	Approved
0.7113	Intermediate Similarity	NPD6098	Approved
0.7111	Intermediate Similarity	NPD4058	Approved
0.7111	Intermediate Similarity	NPD6926	Approved
0.7111	Intermediate Similarity	NPD6924	Approved
0.7111	Intermediate Similarity	NPD4687	Approved
0.7111	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6050	Approved
0.71	Intermediate Similarity	NPD5693	Phase 1
0.7094	Intermediate Similarity	NPD7492	Approved
0.7079	Intermediate Similarity	NPD5276	Approved
0.7079	Intermediate Similarity	NPD4243	Approved
0.7071	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD5988	Approved
0.7041	Intermediate Similarity	NPD3573	Approved
0.7034	Intermediate Similarity	NPD6616	Approved
0.7034	Intermediate Similarity	NPD6336	Discontinued
0.7033	Intermediate Similarity	NPD3703	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data